Methanol → 2-(4-Cyclopropylphenyl)acetic acid

HRID 1913422Notes

Reaction equation

HRID 1913422 reaction equation
C[O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:13][CH2:12]2)=[CH:7][CH:6]=1.CO.[OH-].[Na+]>C1COCC1>[CH:11]1([C:8]2[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:14])=[O:2])=[CH:6][CH:7]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 66845395Methyl(4-cyclopropylphenyl)acetate

Product 1

HCID 204905282-(4-Cyclopropylphenyl)acetic acidYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl(4-cyclopropylphenyl)acetate (710 mg, 3.73 mmol) was dissolved in 5 mL THF, 5 mL MeOH, and aqueous 1N NaOH (7.46 mmol) and the resulting mixture was heated at 45° C. overnight. After cooling to ambient temperature, the reaction was concentrated in vacuo and the residue was diluted with water (50 mL). The aqueous material was acidified with 1N HCl to pH˜3. A light brown precipitate formed which was collected by filtration and dried in a vacuum oven for 3 days to give (4-cyclopropylphenyl)acetic acid (SM-1ag, 395 mg, 60%). MS (ES−) 175.2 (M−H). 1H NMR (DMSO-d6) δ 0.57-0.61 (m, 2H), 0.86-0.91 (m, 2H), 1.81-1.88 (m, 1H), 3.45 (s, 2H), 6.97 (d, 2H), 7.08 (d, 2H), 12.20 (br s, 1H).

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. additionthe residue was diluted with water (50 mL)
  3. customA light brown precipitate formed which
  4. filtrationwas collected by filtration
  5. customdried in a vacuum oven for 3 days

Sources & evidence

ORD record
ord-c04158598db546e0a6dd933494e36fb3
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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